Phloretin

ABSTRACT

Provided herein is a method of reducing the off-taste of a food or beverage wherein the off-taste is selected from the group consisting of licorice, astringency, bitterness and sweet lingering comprising adding about 10 to about 40 ppm, phloretin to the food or beverage wherein the phloretin is provided in the substantial absence of a bitterness-masking aroma substance selected from the groups consisting of homoeriodictylol, homoeriodictyol sodium salt, homoeriodictylol potassium salt or mixtures thereof and wherein the phloretin does not significantly enhance the sweetness of the article or composition.

FIELD

The inventions described herein have use in foods and beverages,particularly those that rely on sweeteners and other flavor componentsand more particularly those that might rely on compounds and ingredientsfound in nature.

BACKGROUND

Phloretin has been reported for use as a modulator of sweetness.

SUMMARY

Provided herein is a method of reducing the off-taste of a food orbeverage wherein the off-taste is selected from the group consisting oflicorice, astringency, bitterness and sweet lingering comprising addingabout 10 to about 40 ppm, phloretin to a flavored article or flavoringcomposition wherein the article or composition is provided in thesubstantial absence of a bitterness-masking aroma substance selectedfrom the groups consisting of homoeriodictylol, homoeriodictyol sodiumsalt, homoeriodictylol potassium salt or mixtures thereof and whereinthe phloretin does not significantly enhance the sweetness of thearticle or composition.

Further provided herein is a method of reducing the off-taste of a foodor beverage wherein the off-taste is selected from the group consistingof licorice, astringency, bitterness and sweet lingering comprisingadding about 10 to about 40 ppm, phloretin to a food or beverage whereinthe food or beverage is provided in the substantial absence of abitterness-masking aroma substance selected from the groups consistingof homoeriodictylol, homoeriodictyol sodium salt, homoeriodictylolpotassium salt or mixtures thereof and wherein the phloretin does notsignificantly enhance the sweetness of the food or beverage. p Furtherprovided herein is the use of phloretin (also known as3-(4-hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)propan-1-one) as a tastemodulator; more specifically, as a masker of off-notes associated withhigh potency sweeteners such as steviol glycosides and rebaudiosides,

Further provided herein is the use of phloretin as a flavor modifier.

BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1 shows the effect of Phloretin on Strawberry Yogurt sweetened withStevia, SG95

FIG. 2 shows the effect of 35 ppm Phloretin when added to PomegranateJuice.

FIG. 3 shows the effect of 30 ppm Phloretin added to sucrose

FIG. 4 shows the effect of Phloretin on the bitterness and astringencyof a sucrose (5%) and stevia (SG95@25 ppm sweetened tropical juice drink

FIG. 5 shows the effect of Phloretin at 30 ppm on the astringency andoff-tastes of a pea protein formulation.

DETAILED DESCRIPTION

For the descriptions herein and the appended claims, the use of “or”means “and/or” unless stated otherwise. Similarly, “comprise,”“comprises,” “comprising” “include,” “includes,” and “including” areinterchangeable and not intended to be limiting.

It is to be further understood that where descriptions of variousembodiments use the term “comprising,” those skilled in the art wouldunderstand that in some specific instances, an embodiment can bealternatively described using language “consisting essentially of” or“consisting of.”

In one embodiment, Phloretin is provided in a food or beverage in anamount of about 15 ppm to about 35 ppm, more particularly from about 20ppm to about 30 ppm, even more particularly at about 20 ppm by weight ofthe total weight of the food or beverage.

In one embodiment, Phloretin modifies the off-note perception of foodand beverages that contain a natural sweetener for example, but notlimited to stevia extracts and luo han guo extracts.

In one embodiment, Phloretin modifies sensory traits, for example bydecreasing the off-note perception of natural, high intensity sweetenersas well as masking other negative flavor properties such as bitterness,licorice, and/or sourness.

It has been discovered that Phloretin, when tasted in water or in amodel beverage solution of water and citric acid contains (for the mostpart) nearly no flavor on its own. However, when used as a tastemodifier in foods and beverages containing steviol glycosides andrebaudioside, phloretin provides off-note masking abilities such asreduced linger, reduced licorice and reduced bitterness.

Higher levels of phloretin do not appear to bring much additional tastemodification benefits and at the same time, higher levels may be evenless effective in masking the bitterness or lingering licorice, andoff-notes associated with some high potency sweeteners.

In on embodiment, phloretin is provided in an amount sufficient toconfer, enhance, improve or modify the flavor or aroma of a food orbeverage.

In one embodiment, the sweetener provided herein is selected from thegroup consisting common saccharide sweeteners, e.g., sucrose, fructose(e.g., D-fructose),glucose (e.g., D-glucose); sweetener compositionscomprising natural sugars, such as corn syrup (including high fructosecorn syrup) or other syrups or sweetener concentrates derived fromnatural fruit and vegetable sources; semisynthetic “sugar alcohol”sweeteners such as erythritol, isomalt, lactitol, mannitol, sorbitol,xylitol, maltodextrin, glycerol, threitol, arabitol, ribitol, anddulcitol; artificial sweeteners such as miraculin, aspartame,superaspartame, saccharin, saccharin-sodium salt, acesulfame-K,cyclamate, sodium cyclamate, and alitame; other sweeteners such astrehalose, melizitose, melibiose, raffinose, palatinose, Iactulose,cyclamic acid, mogroside, tagatose (e.g., D-tagatose), maltose,galactose (e.g., D-galactose), L-rhamnose, D-sorbose, maunose (e.g.,D-maunose), lactose, L-arabinose, D-ribose, D-glyceraldehyde, curculin,brazzein, mogroside, Neohesperidin dihydrochalcone (NHDC), neotame andother aspartame derivatives, D-tryptophan, D-Ieucine, D-threonine,glycine, D-asparagine, D-phenylalanine, L-proline, maltitol,hydrogenated glucose syrup (HGS), magap, sucralose, lugduname,sucrononate, sucrooctate, monatin, phyllodulcin, hydrogenated starchhydrolyzate (HSH), stevioside, rebaudioside A, rebaudioside D,rebadioside M, and other sweet Stevia based glycosides, lo han guo,thaumatin, monellin, carrelameand amd other guanidine-based sweeteners.Particularly, the sweetener is a high potency sweetener, particularly itis selected from the group consisting of saccharin, aspartame,cyclamate, sucralose, saccharine, stevia, rebauasdioside A, neotame,acesulfame K, sucrose, glucose fructose and sorbitol, more particularlyit is selected from the group consisting of fructose and stevia.

In a further embodiment the sweetener is selected from the groupconsisting of sucrose, fructose, and stevia. In a further embodiment,the sweetener comprises a purified stevia extract having a high puritycombination of nine sweet steviol glycosides found within the stevialeaf. The purified stevia extract may be represented by high puritycombination of nine sweet steviol glycosides found within the stevialeaf wherein Reb A accounts for over half of the final composition(e.g., SG95 sold by PureCircle).

Optional ingredients include sucrose, HFCS, steviol glycosides,rebaudiosides, Luo han guo, other high potency sweeteners, and anycombination thereof in the presence of phloretin at 10-50 ppm.

Highly astringent foods and beverages or other products that may becandidates where phloretin may be applied to reduce that flavorcharacteristic.

In one embodiment, provided herein is:

-   i) a flavor comprising Phloretin as described herein and-   ii) a foodstuff base.

For the sake of clarity, it has to be mentioned that, by “foodstuff” wemean here an edible product, e.g. a food or a beverage. Therefore, aflavored article according to the invention comprises 1-Ethoxyethylacetate, as well as optional benefit agents, corresponding to a flavoror aroma and flavor or aroma profile of the desired edible product. Thecompositions and methods provided herein have use in food or beverageproducts. When the food product is a particulate or powdery food, thedry particles may easily be added thereto by dry-mixing. Typical foodproducts are selected from the group consisting of an instant soup orsauce, a breakfast cereal, a powdered milk, a baby food, a powdereddrink, a powdered chocolate drink, a spread, a powdered cereal drink, achewing gum, an effervescent tablet, a cereal bar, and a chocolate bar.The powdered foods or drinks may be intended to be consumed afterreconstitution of the product with water, milk and/or a juice, oranother aqueous liquid.

Suitable foodstuff bases, e.g. foods or beverages, include dairy andconfectionary products where a fresh or fruity tonality is desired.

In another embodiment provided herein is a fluid dairy product includingwithout limitation, non-frozen, partially frozen and frozen fluid dairyproducts such as, for example, milks, ice creams, sorbets and yogurts.

Beverage products include, without limitation, carbonated soft drinks,including cola, lemon-lime, root beer, heavy citrus (“dew type”), fruitflavored and cream sodas; powdered soft drinks, as well as liquidconcentrates such as fountain syrups and cordials; coffee andcoffee-based drinks, coffee substitutes and cereal-based beverages;teas, including dry mix products as well as ready-to-drink teas (herbaland tealeaf based); fruit and vegetable juices and juice flavoredbeverages as well as juice drinks, nectars, concentrates, punches and“ades”; sweetened and flavored waters, both carbonated and still;sport/energy/health drinks; alcoholic beverages plus alcohol-free andother low-alcohol products including beer and malt beverages, cider, andwines (still, sparkling, fortified wines and wine coolers); otherbeverages processed with heating (infusions, pasteurization, ultra hightemperature, ohmic heating or commercial aseptic sterilization) andhot-filled packaging; and cold-filled products made through filtrationor other preservation techniques. The nature and type of theconstituents of the foodstuffs or beverages do not warrant a moredetailed description here, the skilled person being able to select themon the basis of his general knowledge and according to the nature ofsaid product.

The compositions and methods provided herein have use in food orbeverage products. When the food product is a particulate or powderyfood, the dry particles may easily be added thereto by dry-mixing.Typical food products are selected from the group consisting of aninstant soup or sauce, a breakfast cereal, a powdered milk, a baby food,a powdered drink, a powdered chocolate drink, a spread, a powderedcereal drink, a chewing gum, an effervescent tablet, a cereal bar, and achocolate bar. The powdered foods or drinks may be intended to beconsumed after reconstitution of the product with water, milk and/or ajuice, or another aqueous liquid.

The food product may be selected from the group consisting ofcondiments, baked goods, powdery food, bakery filings and Fluid dairyproducts.

Condiments include, without limitation, ketchup, mayonnaise, saladdressing, Worcestershire sauce, fruit-flavored sauce, chocolate sauce,tomato sauce, chili sauce, and mustard.

Baked goods include, without limitation, cakes, cookies, pastries,breads, donuts and the like.

Bakery fillings include, without limitation, low or neutral pH fillings,high, medium or low solids fillings, fruit or milk based (pudding typeor mousse type) fillings, hot or cold make-up fillings and nonfat tofull-fat fillings.

Fluid dairy products include, without limitation, non-frozen, partiallyfrozen and frozen fluid dairy products such as, for example, milks, icecreams, sorbets and yogurts.

Beverage products include, without limitation, carbonated soft drinks,including cola, lemon-lime, root beer, heavy citrus (“dew type”), fruitflavored and cream sodas; powdered soft drinks, as well as liquidconcentrates such as fountain syrups and cordials; coffee andcoffee-based drinks, coffee substitutes and cereal-based beverages;teas, including dry mix products as well as ready-to-drink teas (herbaland tealeaf based); fruit and vegetable juices and juice flavoredbeverages as well as juice drinks, nectars, concentrates, punches and“ades”; sweetened and flavored waters, both carbonated and still;sport/energy/health drinks; alcoholic beverages plus alcohol-free andother low-alcohol products including beer and malt beverages, cider, andwines (still, sparkling, fortified wines and wine coolers); otherbeverages processed with heating (infusions, pasteurization, ultra hightemperature, ohmic heating or commercial aseptic sterilization) andhot-filled packaging; and cold-filled products made through filtrationor other preservation techniques. SG95 is a natural, high puritycombination of nine sweet steviol glycosides found within the stevialeaf. Reb A accounts for over half of the final composition.

The nature and type of the flavoring co-ingredients present in the basedo not warrant a more detailed description here, the skilled personbeing able to select them on the basis of his/her general knowledge andaccording to intended use or application and the desired organolepticeffect. In general terms, these flavoring co-ingredients belong tochemical classes as varied as alcohols, aldehydes, ketones, esters,ethers, acetates, nitriles, terpenoids, nitrogenous or sulphurousheterocyclic compounds and essential oils, and said perfumingco-ingredients can be of natural or synthetic origin. Many of theseco-ingredients are in any case listed in reference texts such as thebook by S. Arctander, Perfume and Flavor Chemicals, 1969, Montclair,N.J., USA, or its more recent versions, or in other works of a similarnature, as well as in the abundant patent literature in the field offlavor. It is also understood that said co-ingredients may also becompounds known to release in a controlled manner various types offlavoring compounds.

By “flavor carrier” we mean here a material which is substantiallyneutral from a flavor point of view, insofar as it does notsignificantly alter the organoleptic properties of flavoringingredients. The carrier may be a liquid or a solid.

Suitable liquid carriers include, for instance, an emulsifying system,i.e. a solvent and a surfactant system, or a solvent commonly used inflavors. A detailed description of the nature and type of solventscommonly used in flavor cannot be exhaustive. Suitable solvents include,for instance, propylene glycol, triacetin, triethyl citrate, benzylicalcohol, ethanol, vegetable oils or terpenes.

Suitable solid carriers include, for instance, absorbing gums orpolymers, or even encapsulating materials. Examples of such materialsmay comprise wall-forming and plasticizing materials, such as mono, di-or trisaccharides, natural or modified starches, hydrocolloids,cellulose derivatives, polyvinyl acetates, polyvinylalcohols, proteinsor pectins, or yet the materials cited in reference texts such as H.Scherz, Hydrokolloids: Stabilisatoren, Dickungs- and Gehermittel inLebensmittel, Band 2 der Schriftenreihe Lebensmittelchemie,Lebensmittelqualität, Behr's VerlagGmbH & Co., Hamburg, 1996.Encapsulation is a well known process to a person skilled in the art,and may be performed, for instance, using techniques such asspray-drying, agglomeration, extrusion, coacervation and the like.

In embodiment, the particular types of end products useful are: flavoredwaters, soft drinks, diet drinks, juice containing drinks, tea andcoffee drinks, alcoholic drinks, neutraceutical drink preparations,medicinal drink formulations, beverage supplements and others foodstuffssuch as dairy drinks, yogurts, cereals, condiments, puddings, gelatins,or any other foodstuffs sweetened with sugar, HFCS, or high potencysweeteners.

The below examples are illustrative only and are not meant to limit theclaims or embodiments described herein.

EXAMPLES Example 1

The addition of 20 ppm Phloretin to a strawberry Yogurt sample sweetenedwith 250 ppm Stevia was judged to be significantly lower in licoricetaste and higher in Strawberry flavor intensity than the control productwhich was also sweetened with 250 ppm Stevia. See Table 1 and FIG. 1.

TABLE 1 Description Flavor Control: Base “full Stevia” (0% sugar, 250ppm Stevia (SG95)) Test: “full Stevia” + 20 ppm Phloretin Test SteviaAttribute Control Stevia @250 ppm + n = 29 @250 ppm 20 ppm PhloretinP-Value Strawberry Flavor * 3.38 3.56 0.0398 Sweetness 3.38 3.38 0.5Acidity 2.88 2.56 0.1753 Licorice (*) 2.69 1.44 0.0518 Fruity 3.5 3.250.1904 Green 2.19 2.38 0.3058 Jammy 3.06 3.19 0.3131 Long Lasting 3 2.560.1699

Example 2

Adding 35 ppm Phloretin to a Pomegranate juice sweetened with 150 ppmStevia, significantly reduces the Sourness and Bitterness Intensity,while significantly increasing the Pomegranate flavor intensity. SeeTable 2 and FIG. 2.

TABLE 2 Pomegranate Juice with Phloretin sensory result Sample 2 Sample1 Pom Juice Pom Juice (Mkt sample (Mkt sample POM Brand) + POM Brand) +SG95 @150 ppm + Attribute SG95 @150 ppm Phloretin @ 35 ppm P-ValuePomegranate Flv 6.12 6.68 0.0977 intensity (*) Sweetness intensity 5.165.79 0.1244 Berry Flv intensity 5.72 6.01 0.4268 Sourness intensity *5.58 4.75 0.0402 Astringent 4.43 4.1 0.2688 Bitterness * 3.85 3.350.0387

Example 3

Adding 30 ppm Phloretin to a Tropical Flavored, sugar sweetened, softdrink containing 7% sucrose significantly reduced its acidity/sourness,bitterness and astringency. See Table 3 and FIG. 3.

TABLE 3 Description Flavor Control: Base (7% sucrose) Test: 7% Sucrose +30 ppm Phloretin Sample 1 Sample 2 Full Sugar 30 ppm Attribute IntensityControl Phloretin P-Value Overall Flavor 6.54 6.76 0.2892 TropicalFlavor 6.33 6.55 0.4635 Mango Flavor 5.72 6.04 0.2545 Passion FruitFlavor 5.96 5.69 0.531 Acidity/Sourness * 4.09 a 3.27 b 0.022Bitterness * 2.58 a 1.9 b 0.0316 Astringency ** 2.9 a 2.05 b 0.0069Off-Note 1.58 1.72 0.6338

Example 4

Adding 30 ppm Phloretin to a Tropical Juice Flavored, sugar (5%) andStevia (25 ppm) sweetened, juice containing soft drink significantlyreduced its bitterness and astringency. See Table 4 and FIG. 4.

Base (Control) Recipe Sugar 70.55 g Citric Acid 1.75 g Ascorbic Acid0.15 g Potassium Sorbate 0.15 g Tropical Compound 050002 JC20181 32.00 gWater 928.40 g Total 1032.86 g

TABLE 4 Sucrose (5%) Test Sample - and Stevia (25 ppm) Control +sweetened Control Phloretin @ 30 ppm P-value Overall Flavor 3.29 3.710.2 Sweetness 2.36 2.29 0.846 Acidity 3.21 2.93 0.522 Bitterness * 1.290.57 0.047 Astringency * 1.71 1.21 0.038 Off-notes 0.93 1.21 0.356Long-lasting (sweet) 1.00 0.50 0.134

Example 5: 1—Objectives

To evaluate sensory effect of phloretin on pea protein solution

2—Approach

Evaluation in blind and randomized conditions of pasteurized sweet watersolution of pea protein isolate

-   -   1. Control: no phloretin added    -   2. Test: 30 ppm phloretin added (via a presolution 10% in        propylene glycol)

3—Formulations and Preparation 3.1 Formulation

TABLE 5 Ingredient Control (% by weight) Test (% by wight) Deionizedwater 94 93.97 Propulse S 3 3 Sugar 3 3 Phloretin (10% 0.03 Propyleneglycol Total 100 100 (1) Propulse S: pea protein isolate: proteincontent 82.35%, fat <0.5%

3.2 Preparation

Weigh and premix protein with sugar (600 gram preparation)

Dispersion/solubilisation of protein-sugar-water to obtain a “mothermixture”: disperse mix protein/sugar in water (becher-deionized water40° C.-Mini Ultra-Turrax T18-Speed 2-time: 7 minutes). The same “mothermixture” for both the Control and Test trials.

Add phloretin (fresh dilution 10% in propylene Glycol) in Test trial.Split each trials in 2 glass bottles: 100 g for pre-evaluation andgeneration of sensory attributes-200 gram for sensory assessment

Pasteurisation (water bach-95° C.-30 minutes). Cooling bottles at roomtemperature-Storage in fridge until tasting. Perform Sensory assessmentat room temperature.

4—Sensory Assessmement 4.1 Sensory Protocol

Eight panelists were asked to rate intensity of sensory attributes usinga 0 to 5 structured scale (from 0 ‘not perceptible’ to 5 ‘strongintensity’). Sensory descriptors were selected to assess taste, tactileand aromatic stimuli Data treatment was run with XLSTAT software (Duncanmean comparison test). Sensory attributes were selected during apreliminary series of applications evaluated in a free-description mode

Symbols for significant differences ! at 90%, * at 95%, ** at 99% and*** at 99.9% confidence (See FIG. 5).

4. Sensory Results

Symbols for significant differences ! at 90%, * at 95%, ** at 99% and*** at 99.9% confidence.

Samples with same letter are not significantly different according toDuncan comparison test. Addition of phloretin (30 ppm as consumed via apre-dilution 10% in propylene glycol) in Test trial was found tosignificantly reduce scores in “astringency” and “off-tastes”. Othersensory attributes related to taste (“Sweetness”, “Bitterness”), tactile(mouthcoating) or aromatic stimuli (“cereal”) were unmodified. See FIG.5.

1-6. (canceled)
 7. A method of reducing astringency of pea protein, themethod comprising introducing phloretin to a flavored article, whereinthe flavored article comprises pea protein.
 8. The method of claim 7,wherein phloretin is introduced to the flavored article at aconcentration ranging from 10 ppm to 40 ppm.
 9. The method of claim 7,wherein the flavored article is a powdered food product.
 10. The methodof claim 7, wherein the flavored article comprises a flavor carrier. 11.The method of claim 10, wherein the flavor carrier is a solid flavorcarrier.
 12. The method of claim 7, wherein the flavored articlecomprises a sweetener.